George Clooney has famously said that he'll never marry again, and his most recent breakup, this time from former WWE star Stacy Keibler, shows that he may just be right. (The Oscar winner, 52, was married once, to actress Talia Balsam, from 1989 to 1993.) "I gave it a shot," he told Piers Morgan in 2011 of wedded bliss, "[And that ought to have] proven how good I was at it." But that certainly doesn't mean he doesn't date! Take a look at Hollywood's most eligible bachelor's past romances.
|Stacy Keibler, 2011-2013|
Keibler made her big debut as Clooney's girlfriend mid-2011, and the two were inseparable for more than a year before work commitments kept them apart. Finally, Keibler pulled the plug on the relationship, though a source tells ABC News that the decision "had nothing to do with kids or wanting to get married." They remain friends.
|Elisabetta Canalis, 2009-2011|
After a two-year relationship, Clooney released a statement that he and Italian actress Canalis had split. "It's very difficult and very personal," the statement read. "We hope everyone can respect our privacy." Afterward, Canalis explained that the relationship ended because of their "personal needs." "He's been special for me," she said. "Very important, just as a father would be."
|Sarah Larson, 2007-2008|
After meeting at his birthday party in Las Vegas, the former cocktail waitress accompanied Clooney to the Oscars and to film festivals. "George is a great guy, a wonderful person," she told Hello! magazine after their split. "We still remain friends and have kept in touch. ... I will always miss his extraordinary dance moves."
|Lisa Snowdon, 2000-2005 (on and off)|
After Clooney met the British model while taping a commercial in Spain, the two dated on and off for about five years. "I sometimes think it will be written on my tombstone – 'George Clooney once dated Lisa Snowdon,'" Snowdon joked to the Mirror newspaper earlier this year. "I'm so used to the 'George thing' that I take it all with a pinch of salt. Of course I understand the fascination. George is fit, women love him, yet he's still a guys' guy, so people are fascinated by him!"
|Celine Balitran, 1996-1998|
According to People, Clooney met Balitran, a French law student and waitress, while he was filming "The Peacemaker." She followed him to L.A., where they dated for three years until she ended things. "She lasted as long as I think she was going to last," he told Esquire magazine at the time, adding that his work schedule also complicated things. "It was like, 'I don't really think I want to play anymore.' "
|Karen Duffy, 1995|
Clooney's relationship with the MTV star was short-lived (though she did hit the Emmy Awards with him in 1995), but their friendship has lasted for quite a while. Not only did she go boating with Clooney and Canalis in 2010, but she also vacationed with the movie star and Keibler last year.
|Talia Balsam, 1989-1992|
They dated briefly in the mid-'80s, but in 1989 the budding TV star and Balsam tied the knot in Las Vegas. "I probably – definitely – wasn't someone who should have been married at that point," he confessed to Vanity Fair after their split. "I just don't feel like I gave Talia a fair shot."
|Kelly Preston, 1987-1989|
Before she married John Travolta, Preston was so serious with Clooney that they lived together -- and shared custody of a potbellied pig named Max. So what made them click? "He's got a great bod," she joked to People magazine. "She drives a Jag," he added.